The largest database of trusted experimental protocols
> Chemicals & Drugs > Organic Chemical > Sulfonamides

Sulfonamides

Sulfonamides are a class of synthetic antimicrobial agents that inhibit bacterial growth by interfering with the synthesis of folic acid.
They are widely used in the treatment of various bacterial infections, including urinary tract infections, pneumonia, and meningitis.
Sulfonamides work by competitively inhibiting the enzyme dihydropteroate synthase, which is essential for bacterial folate production.
This disrupts the bacteria's ability to synthesize DNA and other vital cellular components, leading to their demise.
Research into the development and optimization of sulfonamide drugs is an important area of pharmaceutical science, and the PubCompare.ai platform can enhance such studies by providing access to a wide range of protocols and facilitating comparisons to identify the most effective approaches. [Typo: 'folic' instead of 'folate']

Most cited protocols related to «Sulfonamides»

In total, 150 isolates covering three species were included in the study: E. coli (n =50) and Salmonella (n =50) isolates from the in-house strain collection at the National Food Institute and C. jejuni (n =50) isolates from the in-house strain collection at Statens Serum Institut. The isolates were selected on the basis of having both WGS data and phenotypes available. The Salmonella isolates included strains from 10 different serovars (Tables S1 to S3, available as Supplementary data at JAC Online). All bacterial isolates were sequenced using the Miseq platform (Illumina) to obtain paired-end sequences and assembled de novo using Velvet (reference software). Bacterial strains were screened for phenotypic resistance using MIC determinations interpreted according to EUCAST (www.eucast.org). Only the susceptibility tests relevant for antimicrobial resistance associated with chromosomal point mutations for each species were analysed (Table 2). As resistance to some of the antimicrobial agents can be caused by either acquired genes or chromosomal point mutations, ResFinder-2.1 (www.genomicepidemiology.org)31 (link) was used to detect known acquired resistance genes in the WGS data, using a threshold of 98% identity (%ID) and 60% length (minimum percentage length of the resistance gene to be covered). All isolates with disagreement between the phenotypic and predicted susceptibility were re-tested.

Antimicrobial agents used for susceptibility tests for each species

SpeciesAntimicrobial agents
E. coliciprofloxacin, nalidixic acid, colistin, sulphonamide, tetracycline, spectinomycin
Salmonellaciprofloxacin, nalidixic acid, colistin, spectinomycin
C. jejuniciprofloxacin, nalidixic acid, erythromycin, spectinomycin

Acquired resistance genes, chromosomal point mutations or both can cause resistance to antimicrobial agents.

Publication 2017
Bacteria Chromosomes Colistin Drug Resistance, Microbial Erythromycin Escherichia coli Food Genes Microbicides Nalidixic Acid Phenotype Point Mutation Salmonella Serum Strains Sulfonamides Susceptibility, Disease Tetracycline
The second dataset, published by Holt et al. [24 (link)], consists of 130 globally distributed genomes of Shigella sonnei (Table S2), a Gram-negative bacterium that is a causative agent of dysentery. It enabled a comparison of ARIBA, SRST2, and KmerResistance with the manual method employed in the study of Holt et al. [24 (link)], confirming the accuracy of ARIBA for identifying known resistance SNPs as well as the presence or absence of genes of interest.
The phenotypic resistance profile for a number of antimicrobials is known for each isolate, and is attributable to both acquired resistance genes and SNPs. The three tools were run on all 130 samples using the reference database from CARD, version 1.1.2. To ensure our results were comparable with those originally reported in Table S1 of Holt et al. [24 (link)], we manually added those AMR genes listed on page 4 of their supplementary text not already included in the database (Table S3). The AMR determinants originally reported in the study of Holt et al. [24 (link)] were identified from mapping data, and reported as the proportion of bases in the gene sequence that were covered by reads from each isolate. From these originally reported data, we used a cut-off of >90 % to indicate that a gene was present by their method.
In order to interpret the output of each tool as an AMR call, the following rules were used, where all relevant genes are listed in Table S4. A gene was counted as present by ARIBA if ariba summary reported yes or yes_nonunique; present by KmerResistance if it appeared in its output file; and present by SRST2 if it was reported without a ‘?’.
The focus for the genes of interest for each AMR call were those originally identified and reported in Holt et al. [24 (link)]. Given that the discovery and classification of AMR gene variants is an ongoing process, an AMR gene was called as present if it was either the originally identified gene in Holt et al. [24 (link)], or in the same CD-HIT cluster. Genes conferring resistance to antimicrobials not examined in the original paper were excluded, as were genes conferring resistance to the antimicrobials examined in the paper but falling in different CD-HIT clusters from the originally identified genes. For each antimicrobial examined, an AMR call for a resistant genotype was identified using the following rules. Ampicillin (Amp): the presence of any gene from a set of blaTEM, blaCTX-M and blaOXA genes. Chloramphenicol (Cmp): the presence of any gene from a set of cat genes. Nalidixic acid (Nal): the gyrA gene present, together with one of the SNPs S83L, D87G, or D87Y. Streptomycin (Str): both of the strA and strB genes, or one of the aadA genes. Sulfonamides (Sul): any gene from the set of sul1 and sul2 genes. Tetracycline (Tet): both of tetA +tetR, or all of tetA, C, D, R, where each of the two sets of tetA and tetR genes are disjoint. Trimethoprim (Tmp): any one of a set of dfrA or dhfr genes.
Publication 2017
4,4-difluororetinoic acid Ampicillin Chloramphenicol Drug Resistance, Microbial Dysentery Gene Clusters Genes Genetic Diversity Genome Genotype Gram Negative Bacteria Microbicides Nalidixic Acid Phenotype Shigella sonnei Single Nucleotide Polymorphism Streptomycin Sulfonamides Tetracycline Trientine Trimethoprim
In-house Python scripts based on Openeye’s OEToolkit (Openeye, Santa Fe, USA) were used for compound manipulation and calculating descriptors for the number of heavy atoms, hydrogen-bond donors and acceptors, ring systems, and rotatable bonds. SD files provided by the suppliers were converted into SMILES strings. Protonation and tautomeric states of the compounds were standardised based on predefined substructure patterns to remove duplicates. In silico ADME parameters were calculated using ADMEnsa Interactive (BioFocus DPI, Saffron Walden, UK). Sybyl (Tripos, St. Louis, USA) was used to calculate ClogP values. Compounds containing groups that are charged at physiological pH were neutralised before calculating ClogP values. The ClogP values obtained for compounds where converted to clogD values by equation 1 and a pKa of four was assumed for acetyl-sulfonamides, a pKa of five for carboxylic acids and tetrazoles, a pKa of six for aromatic thiols, and a pKa of nine for amines.

Compounds and their descriptors were stored in a MySQL database and visualised using Vida and the Ogham package (Openeye).
Publication 2007
Amines Carboxylic Acids Donors Hydrogen Bonds physiology Python Saffron Sulfhydryl Compounds Sulfonamides Tetrazoles
Blood samples of 105 domestic Bactrian camels were collected from villages in China (55), MG (28), KAZA (6), RUS (10), and IRAN (6). Blood samples of four dromedaries were also collected from IRAN. The collections were made during routine veterinary treatments with the guidelines from the Camel Protection Association of Inner Mongolia. An endeavor was made to collect samples from unrelated individuals based on the information provided by the owners and local farmers. We collected 50 ml blood for each camel from the jugular vein after disinfection treatment, placed it in EDTA anticoagulant tubes, and then stored it at −80 °C. Ear skin samples (0.5 cm) of 19 wild Bactrian camels were collected from the Great Gobi-Strictly Protected Area A in MG. The wild Bactrian camels chosen were artificially reared and the research was reviewed and approved by the Great Gobi National Park. Proper surgical procedures were adopted in the collection. Local anesthesia (5% procaine hydrochloride) was applied to the ear and the wound was disinfected with iodophor and sulfonamide powder. The samples were eluted with phosphate-buffered saline solutions, placed in cryotubes and were stored at −80 °C.
Publication 2020
Anticoagulants BLOOD Camels Camelus bactrianus Camelus dromedarius Disinfection Edetic Acid Farmers Hydrochloride, Procaine Iodophors Jugular Vein Local Anesthesia Operative Surgical Procedures Phosphates Powder Saline Solution Skin Sulfonamides Wounds
R-ketamine hydrochloride and S-ketamine hydrochloride were prepared by recrystallization of RS-ketamine (Ketalar, ketamine hydrochloride, Daiichi Sankyo Pharmaceutical, Tokyo, Japan) and d-(−)-tartaric acid (or l- (+)-tartaric acid), as described previously.34 The purity of these stereoisomers was determined by a high-performance liquid chromatography (CHIRALPAK IA, column size: 250 × 4.6 mm, mobile phase: n-hexane/dichloromethane/diethylamine (75/25/0.1), Daicel, Tokyo, Japan). NBQX, 2,3-dioxo-6-nitro-1,2,3,4-tetrahydrobenzo[f]quinoxaline-7-sulfonamide (catalog number: 0373, Tocris Bioscience, Bristol, UK, 10 mg kg−1) was dissolved in saline. ANA-12, N2-(2-{[(2-oxoazepan-3-yl) amino]carbonyl}phenyl)benzo[b]thiophene-2-carboxamide (catalog number: BTB06525SC, Maybridge, Trevillett Tintagel, Cornwall, UK, 0.5 mg kg−1) was prepared in vehicle of 1% dimethylsulfoxide in phosphate-buffered saline. The dose of ketamine, NBQX and ANA-12 was selected as reported previously.34 , 35 , 36 (link), 37 (link), 38 (link), 39 (link), 40 (link) Other reagents were purchased commercially.
Publication 2015
2,3-dioxo-6-nitro-7-sulfamoylbenzo(f)quinoxaline diethylamine High-Performance Liquid Chromatographies Ketalar Ketamine Ketamine Hydrochloride Methylene Chloride n-hexane Pharmaceutical Preparations Phosphates Quinoxalines Saline Solution Stereoisomers Sulfonamides Sulfoxide, Dimethyl tartaric acid Thiophene

Most recents protocols related to «Sulfonamides»

Example 1

Monomer M-1 was prepared by mixing 2-(dimethylamino)ethyl methacrylate with pentafluorobenzoic acid in a molar ratio of 1:1. Similarly, Monomers M-2 to M-17 and cM-1 were prepared by mixing a nitrogen-containing monomer with a fluorinated carboxylic acid, fluorinated sulfonamide compound, fluorinated phenol compound, fluorinated β-diketone compound, or unsubstituted benzoic acid (for comparison).

[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
[2] Synthesis of Polymers

Fluorine-containing monomers FM-1 to FM-11 and PAG monomer PM-1 used in the synthesis of polymers have the structure shown below.

[Figure (not displayed)]
[Figure (not displayed)]

Patent 2024
Anabolism Benzoic Acid ethylmethacrylate Fluorine Molar Nitrous Acid pentafluorobenzoic acid Phenols Polymers Sulfonamides

Example 71

[Figure (not displayed)]

A vessel was charged with N-[2,6-difluoro-3-[1-(oxan-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[3,4-b]pyridine-3-carbonyl]phenyl]propane-1-sulfonamide (88.0 mg, 0.149 mmol), 5-bromo-2-(trifluoromethyl)pyrimidine (37.2 mg, 0.164 mmol), potassium fluoride (26.0 mg, 0.447 mmol), bis(triphenylphosphine)palladium(II) dichloride (5.23 mg, 0.00745 mmol) and 0.5 mL 1,4-dioxane/water (4+1). The vessel was evacuated and filled with argon (3×) and heated to 60° C. for 2 h. The reaction was acidified with conc. HCl (0.3 mL), diluted with MeOH (0.2 mL) and heated to 60° C. overnight. After cooling, the reaction was diluted with EtOAc and water. The organic phase was evaporated and the product was purified by flash chromatography (DCM/EtOAc gradient, from 5% to 35% EtOAc) N-[2,6-difluoro-3-[5-[2-(trifluoromethyl)pyrimidin-5-yl]-1H-pyrazolo[3,4-b]pyridine-3-carbonyl]phenyl]propane-1-sulfonamide (42.0 mg, 0.0798 mmol, 54% yield).

Analytical Data:

TLC-MS (ESI): m/z=505.1, 525.1 [M−H]

Patent 2024
Anabolism Argon Blood Vessel Chromatography Dioxanes Palladium potassium fluoride Propane pyridine Pyrimidines Sulfonamides triphenylphosphine

Example 41

[Figure (not displayed)]

1-Methylpiperazine (70 μl, 0.631 mmol) was added to a suspension of ((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)carbamoyl)sulfamoyl chloride (50 mg, 0.159 mmol) in THF (1 mL). The reaction mixture was stirred at room temperature overnight. DMF (1 mL) was added to aid solubility, the mixture was stirred for a further 1 hour, then filtered through a plug of cotton wool and purified by preparative HPLC to afford the title compound (2.8 mg) as a colourless solid.

1H NMR (400 MHz, D2O/NaOD) δ 6.82 (s, 1H), 2.89 (br s, 4H), 2.59 (t, J=7.5 Hz, 4H), 2.48 (t, J=7.3 Hz, 4H), 2.26 (br s, 4H), 1.97 (s, 3H), 1.76 (p, J=7.5 Hz, 4H).

LCMS m/z 379 (M+H)+ (ES+); 377 (M−H) (ES)

Patent 2024
1-methylpiperazine 1H NMR Chlorides Gossypium High-Performance Liquid Chromatographies Lincomycin Piperazine Sulfonamides
Not available on PMC !

Example 74

[Figure (not displayed)]

To a solution of compound 79-1 (50 mg, 0.15 mmol, 1 eq) and propane-2-sulfonamide (29.2 mg, 0.23 mmol, 1.5 eq) in DCM (2 mL) was added EDCI (45.4 mg, 0.23 mmol, 1.5 eq) and DMAP (48.2 mg, 0.39 mmol, 2.5 eq). The mixture was stirred at 19° C. for 1 hr. LCMS showed the starting material was consumed. H2O (10 mL) was added to the solution. The mixture was extracted with ethyl acetate (10 mL*3). The combined organic layers were washed with brine (12 mL*2), dried over anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by prep-HPLC. The title compound (12.3 mg, 29.2 umol, 18.4% yield) was obtained as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 12.28-12.20 (m, 1H), 8.75 (s, 1H), 8.20 (d, J=7.8 Hz, 1H), 7.98-7.92 (m, 3H), 7.86 (s, 1H), 7.75 (d, J=7.8 Hz, 3H), 7.69-7.65 (m, 1H), 3.92-3.83 (m, 1H), 1.35 (d, J=6.8 Hz, 6H).

Patent 2024
1H NMR brine ethyl acetate High-Performance Liquid Chromatographies Lincomycin Propane Sulfonamides Sulfoxide, Dimethyl Vacuum

Example 72

[Figure (not displayed)]

A vessel was charged with N-[2,6-difluoro-3-[1-(oxan-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[3,4-b]pyridine-3-carbonyl]phenyl]propane-1-sulfonamide (80.0 mg, 0.135 mmol), 1-bromo-4-chloro-2-methylbenzene (18.0 μL, 0.135 mmol), potassium fluoride (23.6 mg, 0.406 mmol), bis(triphenylphosphine)palladium(II) dichloride (4.76 mg, 0.00677 mmol) and 0.5 mL 1,4-dioxane/water (4+1). The vessel was evacuated and filled with argon (3×) and heated to 60° C. for 1 h. The reaction was acidified with conc. HCl (0.2 mL), diluted with MeOH (0.2 mL) and heated to 60° C. overnight. After cooling, the reaction was diluted with EtOAc and water. The organic phase was evaporated and the product was purified by flash chromatography (DCM/EtOAc gradient, 0%-40% EtOAc) to yield N-[3-[5-(4-chloro-2-methylphenyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonyl]-2,6-difluorophenyl]propane-1-sulfonamide (32.0 mg, 0.0608 mmol, 45% yield).

Analytical Data:

TLC-MS (ESI): m/z=483.3, 503.3 [M−H]

Patent 2024
Anabolism Argon Blood Vessel Chromatography Dioxanes Palladium potassium fluoride Propane pyridine Sulfonamides Toluene triphenylphosphine

Top products related to «Sulfonamides»

Sourced in United States, Ireland, Australia
The XBridge C18 is a high-performance liquid chromatography (HPLC) column designed for reversed-phase separation of a wide range of analytes. It features a silica-based stationary phase with a C18 alkyl bonding for effective retention and separation of both polar and non-polar compounds.
Sourced in United States, Italy, Japan, Germany
The Gemini C18 is a reversed-phase liquid chromatography column designed for the separation and analysis of a wide range of organic compounds. It features a fully porous silica-based stationary phase with a C18 alkyl bonded ligand. The column is capable of operating at high pressure and temperature conditions, making it suitable for a variety of analytical applications.
Sourced in United Kingdom, United States, Italy, Germany, France, India, Spain, China
Mueller-Hinton agar is a microbiological growth medium used for the antimicrobial susceptibility testing of bacteria. It is a standardized agar formulation that supports the growth of a wide range of bacteria and allows for the consistent evaluation of their susceptibility to various antimicrobial agents.
Sourced in France, Sweden, United States, Germany, United Kingdom, Denmark, Italy, Australia, Spain, Switzerland, Japan
Etest is a quantitative antimicrobial susceptibility testing (AST) method developed by bioMérieux. It provides minimum inhibitory concentration (MIC) values for specific antimicrobial agents. Etest utilizes a predefined antimicrobial gradient on a plastic strip to determine the MIC of a tested microorganism.
Sourced in United Kingdom, United States, China, Germany, Belgium, Italy, Australia
Ampicillin is an antibiotic that is commonly used in microbiology and molecular biology laboratories. It is a broad-spectrum penicillin-type antibiotic that inhibits the synthesis of bacterial cell walls, effectively killing or preventing the growth of susceptible bacteria.
Sourced in United States
The SB-C8 column is a reversed-phase high-performance liquid chromatography (HPLC) column designed for the separation and analysis of a wide range of compounds. The column features a C8 stationary phase, which provides moderate hydrophobicity and is suitable for the analysis of moderately polar to non-polar analytes.
Sourced in France, United States
Ampicillin is a laboratory product that functions as an antibiotic. It is commonly used in molecular biology and microbiology research to selectively culture bacterial cells.
Sourced in United States, United Kingdom, Germany, Canada, France, Belgium, Switzerland, Italy, Spain, China, Ireland, Israel, Sweden, Austria, Australia, Japan, India, Argentina, Denmark, Netherlands, Macao, Brazil, Portugal, Panama
Gentamicin is a laboratory reagent used for the detection and quantification of the antibiotic gentamicin in biological samples. It is a commonly used tool in research and clinical settings.
Sourced in United States, Germany, United Kingdom, China, Italy, Sao Tome and Principe, France, Macao, India, Canada, Switzerland, Japan, Australia, Spain, Poland, Belgium, Brazil, Czechia, Portugal, Austria, Denmark, Israel, Sweden, Ireland, Hungary, Mexico, Netherlands, Singapore, Indonesia, Slovakia, Cameroon, Norway, Thailand, Chile, Finland, Malaysia, Latvia, New Zealand, Hong Kong, Pakistan, Uruguay, Bangladesh
DMSO is a versatile organic solvent commonly used in laboratory settings. It has a high boiling point, low viscosity, and the ability to dissolve a wide range of polar and non-polar compounds. DMSO's core function is as a solvent, allowing for the effective dissolution and handling of various chemical substances during research and experimentation.
Sourced in United States, United Kingdom, Germany, France, Sao Tome and Principe, Canada, Israel, Australia, Italy, Japan
Picrotoxin is a chemical compound that acts as a GABA antagonist. It is primarily used in scientific research as a tool to study the function of GABA receptors.

More about "Sulfonamides"

Sulfonamides are a class of synthetic antimicrobial agents, also known as sulfa drugs, that work by inhibiting bacterial growth through interference with folate synthesis.
These versatile compounds are widely used in the treatment of various bacterial infections, including urinary tract infections, pneumonia, and meningitis.
Sulfonamides exert their antimicrobial effect by competitively inhibiting the enzyme dihydropteroate synthase, a crucial component in the bacterial folate production pathway.
This disruption of folate synthesis hinders the bacteria's ability to produce DNA and other essential cellular components, ultimately leading to their demise.
Research into the development and optimization of sulfonamide drugs is a pivotal area of pharmaceutical science.
Techniques such as XBridge C18 and Gemini C18 chromatography, as well as Mueller-Hinton agar and Etest methods, are commonly employed to evaluate the potency and efficacy of sulfonamide compounds.
Additionally, the use of other antimicrobial agents, like Ampicillin and Gentamicin, in combination with sulfonamides can enhance their therapeutic effects.
The PubCompare.ai platform can greatly enhance sulfonamide research by providing access to a wide range of protocols from literature, preprints, and patents, and facilitating AI-driven comparisons to identify the most effective approaches.
This can lead to improved reproducibility, accuracy, and optimization of sulfonamide-based treatments, ultimately benefiting patient outcomes.
Furthermore, the incorporation of solvents like DMSO and compounds like Picrotoxin can play a crucial role in the development and evaluation of sulfonamide-based therapies.
By leveraging the insights and tools provided by PubCompare.ai, researchers can streamline their sulfonamide research and drive advancements in this important area of pharmaceutical science.